Best results for Sailing

Sail Seattle’s harbor and enjoy a brunch buffet on a tall ship

Sail calm waters to spot dolphins and enjoy a Gulf sunset with dancing and games

Book two separate trips: an Alcatraz visit plus a Bay sail on Adventure Cat

Customize a private sail with a USCG-licensed captain for up to 6 guests

Sail into the sunset on an adults-only catamaran cruise with pupus and island-style music

Sail Casco Bay at sunset with live music and a BYOB vibe

Sail Cape Cod Bay on a family-friendly cruise where you can help raise sails and bring a picnic aboard

Spend two days exploring charming North Shore towns with a private sunset sail and landmark stops

Sail the Straits on a catamaran with time to relax, swim, and try stand-up paddleboarding

Cruise Lake Tahoe at sunset with live local music

Friday fireworks sail with front-row views from the water

Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip

Build advanced sailing skills in a 5-day Flying Scot course for ages 8–15

Sail a Catalina 34 and build practical skills in 2.5 hours

Sail Boston Harbor and enjoy freshly shucked oysters onboard

Sail Boston Harbor on a 1.5-hour schooner cruise from Rowes Wharf

Sail into Destin Harbor for a private sunset and fireworks view

Sail into sunset views of Mackinac Island and the Mighty Mackinac Bridge

Sail Cape Cod Bay at sunset on a bring your own food and drinks cruise

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Sail Cape Cod Bay on the historic Schooner Hindu

Charter a private sail in Provincetown for up to 34 guests

Charter a sailboat in Key West for up to 42 guests

Sail Provincetown at sunset on the historic Schooner Hindu